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Synthesis and properties of triethylammonium 2,2,5-triphenyl-1,3,2,5-dioxaborataphosphorinane

  • Organic Chemistry
  • Methods Of Synthesis
  • Published:
Bulletin of the Russian Academy of Sciences, Division of chemical science Aims and scope

Abstract

The reaction of bis(hydroxymethyl)phenylphosphine with isobutyl diphenylborate in the presence of triethylamine leads to the formation of triethylammonium 2,2,5-triphenyl-1,3,2,5-dioxaborataphosphorinane (1). The reaction of compound 1 with electrophilic reagents (O, S, Se, CH2O, RHal) leads to quaternization of the phosphorus atom, giving the corresponding phosphine oxides, sulfides, and selenides and P,B-containing betaines. In the reactions of compound 1 with amines aminomethylphosphines of the diazaphosphorinane and diazadiphosphacyclooctane series are formed. Ammonium 1,3,2,5-dioxaborataphosphorinanes dissociate in solutions and enter into ion exchange with phosphonium iodides, leading to phosphonium 1,3,2,5-dioxaborataphosphorinanes. The latter, in the case of the aminomethylphosphonium cation, undergo intramolecular rearrangement with the formation of P,B-containing betaines and aminomethylphosphines.

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Literature cited

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Authors
  1. G. N. Nikonov
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  2. A. A. Karasik
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  3. B. A. Arbuzov
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Additional information

Deceased.

A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan' Scientific Center, Russian Academy of Sciences, 420083 Kazan'. Translated fromIzvestiya Akademii Nauk, Seriya Khimicheskaya, No. 6, pp. 1398–1405, June, 1992.

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Nikonov, G.N., Karasik, A.A. & Arbuzov, B.A. Synthesis and properties of triethylammonium 2,2,5-triphenyl-1,3,2,5-dioxaborataphosphorinane. Russ Chem Bull 41, 1094–1099 (1992). https://doi.org/10.1007/BF00866594

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  • DOI: https://doi.org/10.1007/BF00866594

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